Sulfuric acid magnesium salt (1:1) → HCID 86584831, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23](=[O:28])N(OC)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].OS([O-])(=O)=O.[K+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH:23]=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -30 °C
Procedure
To 360 ml THF 30.8 ml LiAlH4 solution (30.8 mmol, 1M in THF, 1.2 eq) were added, the solution was cooled to −30° C. and 10.9 g (25.67 mmol) (2S,4R)-4-(4-Methoxy-benzylsulfanyl)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 100 ml THF were added at that temperature, stirred for 30 min. The solution was cooled to −78° C. and a suspension of silica gel, MgSO4 and 10% KHSO4 solution was added, and slowly warmed to RT. The suspension was filtered, thoroughly washed with THF and evaporated. The crude product was redissolved in CH2Cl2 and dried over Na2SO4 and evaporated yielding 9 g (quant.) (2S,4R)-2-Formyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as yellow oil, MS: 351 (M+).
Workup
- temperatureThe solution was cooled to −78° C.
- additionwas added
- temperatureslowly warmed to RT
- filtrationThe suspension was filtered
- washthoroughly washed with THF
- customevaporated
- dissolutionThe crude product was redissolved in CH2Cl2
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-e3935882b6a74b6f9e1aff9c82d63e0d
- Source dataset
- uspto-grants-2003_04
- Patent number
- US06541638B2
Reaction notes
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